Table 2

1H- and 13C-NMR assignments for DAT (2) and its glucosylated metabolite (7)

Table 2
Carbon No.δH2-aδC2-b
2722-c72-d
1——151.1* 152.0*
2——125.4127.4
36.82  (s)* 6.94  (s)* 119.0** 116.0
4——150.8* 151.6*
5——139.3136.5
66.87  (s)* 7.13  (s)* 115.8** 116.0
72.16  (s)2.27  (s)17.616.3
83.23  (m)3.32  (m)28.427.6
91.15 (d, J = 7.2)1.20 (d, J = 6.8)24.923.5
101.15 (d, J = 7.2)1.20 (d, J = 6.8)24.923.5
114.27 (t, J = 4.9)4.16 (t, J = 5.6)66.466.5
123.58 (t, J = 4.9)2.94 (t,J = 5.6)59.458.9
132.992.4445.945.1
14(s)(s)45.945.1
1′—4.96 (J = 7.5)2-e —104.0
2′——75.1
3′—3.48–3.64—78.3*
4′—(m)—71.6
5′——78.1*
6′—3.96 (dd, J = 2, 12.4) —62.7
3.76 (dd,J = 5.6, 12.4)

  • ↵2-a ppm (J = Hz) at 250 MHz in D2O (* or **chemical shift assignments may be reversed).

  • ↵2-b ppm at 62.9 MHz (*chemical shift assignments may be reversed).

  • ↵2-c In D2O.

  • ↵2-d In CD3OD.

  • ↵2-e From 500 MHz spectra and simulations (see text and fig. 6).